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Cheap Flights from Chicago to Oakland $271.82

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Cheapest Flights from Chicago to Oakland (MDW to OAK)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Oakland (MDW to OAK)

Question : Which airline can you expect delays with on this route?
Answer : If you're flying XOJET to Oakland from Chicago, you may be tardy as they're late 100% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : Is there another local airport that can get you to Oakland?
Answer : O'Hare International Airport is just 16 miles away, and, on average, flights are 36% cheaper for the upcoming two months. Save and put that extra money toward your next adventure.

Question : Do travelers from Chicago typically stay in Oakland for very long?
Answer : The average time spent in Oakland by travelers from Chicago is about one week.

Question : About how long is the flight from Chicago to Oakland?
Answer : On average, the flight time from MDW to OAK is four hours and 45 minutes.

Question : Can you cut down on flight costs by changing the day of the week you travel to Oakland?
Answer : The lowest-cost day to fly in May is Saturday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : What is the cheapest day to fly in the next four weeks?
Answer : As of Apr 24th, the best day for booking to Oakland (OAK) is Apr 25th. It costs $246, which is 42% below the average price to book the same route.

Question : In terms of overall promptness, how does MDW to OAK rank compared to the rest of the world?
Answer : Using the combined on-time percentage and average delay breakdown, Chicago to Oakland currently has a 2 out of a possible 5 star rating. A 2-star rating means you should feel rather worried about getting to Oakland on time.